So, this Ask accomplishes a few things for me. First and foremost, it’s an excuse to draw Cloud in his drag look (or, at least, one of them, there appears to be a few variances), something I’ve never done despite liking this look for him for a long time. A second thing it does is allows me to address the idea of using established crossdressing looks for Trap Sluts, something I’ve been avoiding so far. Like Cloud says here, I like presenting new looks for these characters, which is why people like Cloud, Nagisa, and even Ash haven’t shown up in the series yet (and, if they do, they’ll probably have different looks than their canon crossdressing appearances). At least for now, though, I’ve got no shortage of boys who haven’t canonically crossdressed that I want to use for that series.